Chemical Nomenclature

259 Pages·1998·4.367 MB·English

by  E. W. Godly (auth.), K. J. Thurlow (eds.)

Chemical Nomenclature
Chemical Nomenclature
Edited by
K. J. Thurlow
Laboratory of the Government Chemist
Teddington, Middlesex
UK
SPRINGER SCIENCE+BUSINESS MEDIA, B.V.
A c.I.P. Catalogue record for this book is available from the Library of Congress
ISBN 978-94-010-6081-3 ISBN 978-94-011-4958-7 (eBook)
DOI 10.1007/978-94-011-4958-7
AII Rights Reserved
© 1998 Springer Science+Business Media Dordrecht
Originally published by Kluwer Academic Publishers in 1998
No part of the material protected by this copyright notice may be reproduced or
utilized in any form or by any means, electronic or mechanical,
including photocopying, recording, or by any information storage and
retrieval system, without written permission from the copyright owner.
For my parents
Contributors
J. Buckingham Chapman & Hall, 2-6 Boundary Row,
London SEI 8HN, UK
P. E. Childs Dept. of Chemical and Environmental
Sciences, University of Limerick,
Limerick, Ireland
E. W. Godly 10 Lawrence Avenue, New Malden,
Surrey KT3 5LY , UK
A. D. Jenkins The School of Chemistry, Physics and
Environmental Science, University of
Sussex, Falmer, Brighton BN1 9QJ, UK
K. J. Thurlow Chemical Nomenclature Advisory Service,
LGC, Queen's Road, Teddington,
Middlesex TWll OLY , UK
R. B. Trigg British Pharmacopoeia Commission,
Market Towers, 1 Nine Elms Lane,
London SW8 5NQ, UK
s.
B. Walker Mr. S.B. Walker, 45 Windmill Avenue,
Wokingham, Berks RG41 3XA, UK
D. Weisgerber Chemical Abstracts Service, 2540
Olentangy River Road, PO Box 3012,
Columbus, Ohio 43210-0012, USA
Contents
Preface xii
1 The need for good nomenclature 1
E. W. GODLY
References 25
2 From hydrogen to meitnerium: naming the chemical elements 27
P. E. CHILDS
2.1 Introduction 27
2.2 The search for simplicity: the concept of an element 28
2.3 The naming of the elements before 1789 33
2.4 Lavoisier's contribution 33
2.5 Berzelius and the agreement on symbols 35
2.6 Organizing the elements 37
2.7 Isotopes and radioactivity 39
2.8 Choosing names for new elements 41
2.8.1 Elements named after people 42
2.8.2 Elements named after countries or places 43
2.8.3 Named after a distinctive property 44
2.8.4 Named after a mineral 45
2.8.5 Named after a mythological figure 45
2.9 Some cases of elemental confusion 46
2.9.1 Manganese and magnesium 46
2.9.2 Plumb crazy over lead 48
2.9.3 A Hatchett job on niobium 49
2.10 Hydrogen: a special case 51
2.11 Numbering the columns and groups 51
2.12 Naming groups, columns and rows 52
2.13 Spurious elements 53
2.14 No universal names 54
2.15 Variant English spellings and symbols 54
2.16 IUPAC tries to bring order 55
2.17 Conclusion 56
Appendix 2.A Definitions of 'element' down the ages 57
Appendix 2.B Discovery of the elements 58
Appendix 2.C Chronology of the discovery of the elements 62
References 65
viii CONTENTS
3 Chemical Abstracts Service Chemical Substance Index
nomenclature 67
D. W. WEISGERBER
3.1 Introduction 67
3.2 Mission of CAS 68
3.3 History of CAS 68
3.4 Chemical Substance Indexes 71
3.5 Chemical Substance Index nomenclature 73
3.6 Relationship of CAS nomenclature to national and
international authorities 85
3.7 Growth of the chemical literature 88
3.8 CAS registry system 90
3.9 Computer-supported name generation systems 99
3.10 Challenges for the future 101
Bibliography 102
4 IUPAC Nomenclature part 1, organic 103
K. J. THURLOW
4.1 Introduction 103
4.2 Organic names 105
4.2.1 Where do we begin? 105
4.2.2 How do we decide on a name? 106
4.2.3 Unsaturated compounds 115
4.2.4 Unsaturated cyclic compounds 116
4.2.5 Multivalent radicals from unsaturated cyclic
compounds 117
4.2.6 Fusion 117
4.2.7 Bridges 119
4.2.8 Spiro compounds 120
4.2.9 Hydrocarbon ring assemblies 121
4.2.10 Heterocyclic systems 122
4.2.11 Replacement nomenclature 124
4.2.12 Seniority of chains 124
4.2.13 Seniority of rings 125
4.2.14 Indicated hydrogen 125
4.2.15 Other suffixes 126
4.2.16 Summary 126
References 126
5 IUPAC nomenclature part 2, organic, inorganic and others 127
K. J. THURLOW
5.1 Specific examples 127
CONTENTS ix
5.1.1 }\ssenlbly nanles 128
5.1.2 Special systenls 131
5.1.3 Phane nOnlenclature 131
5.1.4 Fullerenes 131
5.1.5 Ions 132
5.2 Stereochenlistry 132
5.2.1 Chirality 133
5.3 Deducing the structure fronl the nanle 136
5.4 Inorganic nanles 136
5.4.1 Sinlple inorganic nanles 137
5.4.2 }\lphabetical order 137
5.4.3 Oxidation and charge nUnlbers 137
5.4.4 Hydrides 138
5.4.5 Coordination cOnlpounds 138
5.4.6 Porphyrins, etc. 142
5.4.7 General problenls 143
5.4.8 SUnlnlary 143
References 145
6 Nomenclature for polymer chemistry 146
A D. JENKINS
6.1 Introduction 146
6.2 The stipulation 147
6.3 PolYnlers and polYnler nlolecules: basic definitions of tefnlS 148
6.4 Regular single-strand, quasi-single-strand and double-
strand polYnlers 150
6.5 PolYnler fOfnlulae 152
6.6 CopolYnlers 152
6.7 Irregular single-strand organic polYnlers 154
6.8 Double-strand organic polYnlers 155
6.9 Non-linear polYnlers 155
6.10 Stereochenlistry 156
6.11 Individual nlacronlolecules, their assenlblies and dilute
polYnler solutions 156
6.12 Crystalline polYnlers and liquid-crystal polYnlers 157
6.13 PolYnlerization reactions 157
6.14 Degradation and ageing 158
6.15 Multi-phase polYnler systenls 158
6.16 Mechanical properties 158
6.17 Current and future projects 159
6.18 Conclusion 159
}\cknowledgenlents 160
References 160
X CONTENTS
7 Natural Products 162
J. BUCKINGHAM
7.1 Introduction 162
7.2 Trivial names 164
7.2.1 Good practice in the assignment of trivial names 167
7.3 'Semi-trivial' names; a class that should be discouraged 169
7.4 Biogenetic numbering and the natural product specialists'
semi-systematic schemes 172
7.5 Systematic nomenclature 175
7.6 IUPAC semi-systematic names 175
7.6.1 Modification of fundamental parent structures 176
7.7 Stereochemical considerations 179
7.7.1 The ent-convention 181
7.8 Review of natural product classes 183
7.8.1 Aliphatic compounds; lipids 183
7.8.2 Aromatic, heteroaromatic and reduced aromatic
systems 183
7.8.3 Carbohydrates; glycosides 186
7.8.4 Tannins 188
7.8.5 Terpenoids 188
7.8.6 Steroids 195
7.8.7 Flavonoids 196
7.8.8 Lignans 198
7.8.9 Amino acids and peptides 199
7.8.10 Alkaloids 200
7.8.11 Polypyrroles 204
7.9 Conclusion 205
References 206
8 Trivial nomenclature: the INN and ISO systems 208
R. B. TRIGG
8.1 Introduction 208
8.2 The INN System 208
8.2.1 Background 208
8.2.2 Secretariat mechanism 209
8.2.3 Guiding principles 213
8.2.4 The 'prefix-stem' approach 214
8.2.5 Stereochemistry 217
8.2.6 Modified INN 219
8.2.7 Radicals and groups 219
8.2.8 Recombinant biological substances 221
8.2.9 Mixtures 223
8.2.10 The trade mark interface and the protection of INN 225
CON1ENTS xi
8.2.11 Computer support 227
8.2.12 Summary 228
8.3 The ISO system 228
8.3.1 Constitution 229
References 234
9 Computer-generated chemical nomenclature 235
S. B. WALKER
Index 243